For some reason I think the maturity level of this conversation has gone down...

I think that although the so called "race card" can help in some cases, your personality/the vibe you give off will make or break you. As for HS girl hmm... I know there are relationships like that which has worked out, but in most cases the girl that do date men much older don't tend to last long and evenutally go back to dating someone around their own age. (Just wondering what is your age difference?)

If you really want to go for her though find out her likes/dislikes, interest/hobbies, to see if you are compatible this will also let you find out if you were just going after her for looks or actually for who she is and vice versa.